Peocess for the preparation of wet



Patented Feb. .1938 I UNI TE 1- 'rES some? PATENT cries PROQESS FOR THE PREPARATION OF WET- THNG,

EMULSHFYING,

DISPERSING R CLEANSING AGENTS AND PRODUCTS OR- TIMNEH) BY THIS PROCESS Andi- Bntignot, Creil, France, assignor to Compagnie Nationale de Matieres Colorantes et Manufactures dc Produits Ghimiques du Nord Runies,

Etablissemcnts Kuhl'mann, France, a corporation of France Paris,

No Drawing. Application April 24, 1935, Serial N0. 13,078. lin'France May 2, 1934 M @laims.

tainedby the known general method consisting in passing over a catalyst a mixture of aliphatic of its weight of iron filings.

Now it has been found in accordance with the present. invention that these ketones can be easily halogenated and that the halogen fixed is specially reactive and can be replaced easily by a solubilizing group or by a chain comprising such a group. The products thus obtained are wetting, emulsifying dispersing or cleansing agents of great value.

As solubilizing groups can be selected for example either solubilizing groups of acid character such as the groups --SO3H, OSO3H, -OPO3H2, in the free state or as salts, or solubilizing groups of basic character such as primary, secondary or tertiary amino groups, preferably as salts, or also solubilizing groups of neutral character such as those constituted by an assembly of hydroxyl groups or ether-oxide groups, although'in this latter case the solubility obtained is probably only a colloidal solubility.

The replacement of the halogen by the solubilizing group may be made in one or more stages. It is possible 'for example toreplace the halogen by a hydroxyl group and to sulphonate the product obtained in such a manner as to obtain a sulphuric acid ester. It is likewise possible to replace the halogen directly by a sulphonic, thicsulphate, amino, diethylamino, poly-glycerine group by treating the halogenated derivative respectively with sodium sulphite, -s'odium hyposulfite, ammonia, diethylamine, a sodium compound of poly-glycerine and so on.

It is also possible; as has been stated above, to 45 replace the halogen by a chain containing a solubiiizing group. This replacement can likewise be effected in one or more stages. It is possible for example to cause the halogenated derivative of the ketone to react with an organic compound 30 containing on the one hand a group capable of reacting with the halogen of the ketone and on the other hand a solubili'zing group or a group capable of being converted into such a group by subsequent reaction. As compounds of this type .5 can be mentioned in particular aminomethaneacid and acetic; acid. The ketones R--C0--R are obtained chiefly by heating a fatty'acid withsulphonic acid, taurine, asymetrical-dimethylethylene-diamine, ethanolamine and so on. the case of ethanolamine the product obtained is to be sulphonated.

The following examples illustrate the invention without limiting the same thereto.

Example 1 There is dissolved in carbon tetrachloride one molecule of a ketone derived from the stearic acid and of the type R--COR where R represents an aliphatic chain saturated with about i8 carbon atoms. There is passed into this solution at cur-- rent of chlorine in quantity corresponding to one molecule, then the hydrochloric acid in excess is removed and the solvent is evaporated. The chlorinated ketone is purified by crystallization in glacial acetic acid.

Example 2 There is dissolved in carbon-tetrachloride one molecule of a ketone derived from the fatty acid of coconut and acetic acid of the formula R.CO-CH3 in which R represents an aliphatic chain of about 13 carbon atoms. Bromine. is added drop by drop in quantity corresponding to one molecule, the hydrobromic acid in excess is removed and the solvent is evaporated. The brominated ketone is purified by distillation in vacuum.

Example 3 The product of Example 2 is heated to-boiling for 3 hours with an aqueous solution containing 20% of sodium sulphite. It passes into solution and gives a soluble product having good foaming,

wetting and cleansing properties.

Example 4 The product of Example 2 is heated gently with the theoretical quantity of alcoholic potash. A product is obtained no longer containing halogen and in which the bromine atom has been replaced by an OH group. This hydroxy-netone can be treated with sulphuric acid or phosphoric acid according to the known methods. The products obtained have good wetting and cleansing properties.

Ewample 5 1 molecular proportion of the product of Exam pie 2 is dissolved in benzene. 2 molecules are added of the finely ground monosodic derivative of the glycerine. There it is heated under reflux for 3-4 hours, poured into water and extracted with benzene. 0n evaporation of the henzenic solution there is obtained a thick oil of clear yellow colour which is the desired poiyhydroxy compound. This product, esterifled by known means withsulphuric acid, gives a cleansing agent of excellent properties.

Ecomple 6 The product of Example 2 is heated to 120 C.

with twice its ii eight of anhydrous aminomethane-sulphonate oi sodium. There is taken up in water and the residue is extracted with benzene. After filtration of the benzenic solution, neutralization evaporation of the benzene there is obtained the desired condensation product containing sulphur and nitrogen.

Eezample 7 The product at 'ii iiample 2 is dissolved in benacne. is current of gaseous ammonia is passed through at ordinary temperature. There is illtered in order to rate the ammonium bromide which is recovered in practically theoretical quan-- tity. The bensenic solution evaporated to dryness gives the desired nitrogen compound.

Ecample 8 or the preparation of wetting, at mg or cleansing agents consisting in mcnon- "ogenating aliphatic ketones of the general in R-CO -CHa, in which R represents an alipl'iatic chain containing from 8 to 18 atoms oi 'arhon, and condensing the halogenated lretone thus obtained with an alkali metal compound.

3. The process for the preparation of wetting, emulsifying,dispersing or cleansing agents consisting in monohalogenating aliphatic ketones of the general formula R-CO--CHa, in which R represents an aliphatic chain containing from 8 to 18 atoms of carbon and condensing the halogenated hetone thus obtained with diethylamine.

i. The wetting, emulsifying, dispersing and cleansing agents obtained by the action oi" an alkali metal compound of glycerine on monohalogenated aliphatic ketones of the general formula M'O-CHIZ, in which R represents an dragon.

aliphatic chain which contains from 8 to 18 atoms I of carbon.

5. The wetting, emulsifying, dispersing and cleansing agents obtained by the action of diethylamine on monohalogenated aliphatic ketones of the general i'ormula'R--CO-CH:, in which R" represents an aliphatic chain which contains from 8 to 18 atoms of carbon.

6. The wetting, emulsifying, dispersing and cleansingagents obtained by the introduction oi a sulphonic group, in place of the halogen, on monohalogenated aliphatic ketones of the general formula R-CO-CH: in which R represents an aliphatic chain which contains from 8 to 18 atoms of carbon.

7. A process for the preparation of wetting, emulsifying, dispersing or cleansing agents, consisting in monohalogenating aliphatic ketones of the general formula R-CO-CHa, in which R represents an aliphatic chain containing from 6 to 18 atoms of carbon and in condensing the halogenated ketones thus obtained with agents containing a solubilizing group and a reactive hy- 8. A process for the preparation of wetting,

emulsifying. dispersing or cleansing agents, con

sisting in monohaiogenating aliphatic ketones of the general formula R-COCHs, in which R represents an aliphatic chain containing from 6 to 18 atoms of carbon and in condensing the halogenated ketones thus obtained with agents containing a solubilizing group and an alkalimetal which replaces a reactive hydrogen.

9. A process for the preparation of wetting,

emulsifying, dispersing or cleansing agents, consisting in monohalogenating ketone mixtures resulting from the fatty acids oi cocoanut oil mixed with acetic acid, and in condensing the halogenated ketones thus obtained with agents containing a, solubiiizing group and a reactive'hydrogen.

10. A process for the preparation of wetting, emulsifying, dispersing or cleansing agents, consisting in monohalogenatlng ketone mixtures rcsulting from the fatty acids oi. cocoanut oil mixed with acetic acid, and in condensing the halo-' genated ketones thus obtained with agents containing a solubilizing group and analkali metal which replaces a reactive hydrogen.

11. The wetting, emulsifying, dispersing and process claimed cleansing agents obtained by the in claim 7. 1

12. The wetting, emulsifying, dispersing and cleansing agents obtained by'the process claimed in claim 8.

13. The wetting, emulsifying, dispersing and cleansing agents obtained'by the process claimed in claim 9.

14. The wetting, emulsifying, dispersing and cleansing agents obtained by the process claimed in claim 10.

nn'onn BU'I'IGNOT. 

